diff --git a/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesButton.tsx b/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesButton.tsx
index acaa042b8..208e13949 100644
--- a/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesButton.tsx
+++ b/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesButton.tsx
@@ -11,7 +11,7 @@ import { observer } from 'mobx-react-lite';
 import { FunctionComponent } from 'preact';
 import { useCallback, useEffect, useRef, useState } from 'preact/hooks';
 import { Icon } from '../Icon';
-import { useCloseOnClickOutside } from '../utils';
+import { useCloseOnBlur } from '../utils';
 import {
   ChallengeReason,
   ContentType,
@@ -66,9 +66,7 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
     const buttonRef = useRef<HTMLButtonElement>(null);
     const panelRef = useRef<HTMLDivElement>(null);
     const containerRef = useRef<HTMLDivElement>(null);
-    useCloseOnClickOutside(containerRef, () => {
-      setOpen(false);
-    });
+    const [closeOnBlur, keepMenuOpen] = useCloseOnBlur(containerRef, setOpen);
 
     const [attachedFilesCount, setAttachedFilesCount] = useState(
       note ? application.items.getFilesForNote(note).length : 0
@@ -170,7 +168,10 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
     const toggleFileProtection = async (file: SNFile) => {
       let result: SNFile | undefined;
       if (file.protected) {
+        keepMenuOpen(true);
         result = await application.protections.unprotectFile(file);
+        keepMenuOpen(false);
+        buttonRef.current?.focus();
       } else {
         result = await application.protections.protectFile(file);
       }
@@ -207,10 +208,13 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
         file.protected &&
         action.type !== PopoverFileItemActionType.ToggleFileProtection
       ) {
+        keepMenuOpen(true);
         isAuthorizedForAction = await authorizeProtectedActionForFile(
           file,
           ChallengeReason.AccessProtectedFile
         );
+        keepMenuOpen(false);
+        buttonRef.current?.focus();
       }
 
       if (!isAuthorizedForAction) {
@@ -354,6 +358,7 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
             className={`sn-icon-button border-contrast ${
               attachedFilesCount > 0 ? 'py-1 px-3' : ''
             }`}
+            onBlur={closeOnBlur}
           >
             <VisuallyHidden>Attached files</VisuallyHidden>
             <Icon type="attachment-file" className="block" />
@@ -374,6 +379,7 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
               maxHeight,
             }}
             className="sn-dropdown sn-dropdown--animated min-w-80 max-h-120 max-w-xs flex flex-col overflow-y-auto fixed"
+            onBlur={closeOnBlur}
           >
             {open && (
               <AttachedFilesPopover
@@ -382,6 +388,7 @@ export const AttachedFilesButton: FunctionComponent<Props> = observer(
                 note={note}
                 handleFileAction={handleFileAction}
                 currentTab={currentTab}
+                closeOnBlur={closeOnBlur}
                 setCurrentTab={setCurrentTab}
                 isDraggingFiles={isDraggingFiles}
               />
diff --git a/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesPopover.tsx b/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesPopover.tsx
index 1515e5307..48b3f034b 100644
--- a/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesPopover.tsx
+++ b/app/assets/javascripts/components/AttachedFilesPopover/AttachedFilesPopover.tsx
@@ -1,3 +1,4 @@
+import { FOCUSABLE_BUT_NOT_TABBABLE } from '@/constants';
 import { WebApplication } from '@/ui_models/application';
 import { AppState } from '@/ui_models/app_state';
 import { ContentType, SNFile, SNNote } from '@standardnotes/snjs';
@@ -22,6 +23,7 @@ type Props = {
   application: WebApplication;
   appState: AppState;
   currentTab: PopoverTabs;
+  closeOnBlur: (event: { relatedTarget: EventTarget | null }) => void;
   handleFileAction: (action: PopoverFileItemAction) => Promise<boolean>;
   isDraggingFiles: boolean;
   note: SNNote;
@@ -33,6 +35,7 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
     application,
     appState,
     currentTab,
+    closeOnBlur,
     handleFileAction,
     isDraggingFiles,
     note,
@@ -100,6 +103,7 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
     return (
       <div
         className="flex flex-col"
+        tabIndex={FOCUSABLE_BUT_NOT_TABBABLE}
         style={{
           border: isDraggingFiles
             ? '2px dashed var(--sn-stylekit-info-color)'
@@ -116,6 +120,7 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
             onClick={() => {
               setCurrentTab(PopoverTabs.AttachedFiles);
             }}
+            onBlur={closeOnBlur}
           >
             Attached
           </button>
@@ -128,6 +133,7 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
             onClick={() => {
               setCurrentTab(PopoverTabs.AllFiles);
             }}
+            onBlur={closeOnBlur}
           >
             All files
           </button>
@@ -144,6 +150,7 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
                   onInput={(e) => {
                     setSearchQuery((e.target as HTMLInputElement).value);
                   }}
+                  onBlur={closeOnBlur}
                 />
                 {searchQuery.length > 0 && (
                   <button
@@ -151,6 +158,7 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
                     onClick={() => {
                       setSearchQuery('');
                     }}
+                    onBlur={closeOnBlur}
                   >
                     <Icon
                       type="clear-circle-filled"
@@ -170,6 +178,7 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
                   isAttachedToNote={attachedFiles.includes(file)}
                   handleFileAction={handleFileAction}
                   getIconType={application.iconsController.getIconForFileType}
+                  closeOnBlur={closeOnBlur}
                 />
               );
             })
@@ -190,7 +199,11 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
                   ? 'No files attached to this note'
                   : 'No files found in this account'}
               </div>
-              <Button type="normal" onClick={handleAttachFilesClick}>
+              <Button
+                type="normal"
+                onClick={handleAttachFilesClick}
+                onBlur={closeOnBlur}
+              >
                 {currentTab === PopoverTabs.AttachedFiles ? 'Attach' : 'Upload'}{' '}
                 files
               </Button>
@@ -204,6 +217,7 @@ export const AttachedFilesPopover: FunctionComponent<Props> = observer(
           <button
             className="sn-dropdown-item py-3 border-0 border-t-1px border-solid border-main focus:bg-info-backdrop"
             onClick={handleAttachFilesClick}
+            onBlur={closeOnBlur}
           >
             <Icon type="add" className="mr-2 color-neutral" />
             {currentTab === PopoverTabs.AttachedFiles
diff --git a/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileItem.tsx b/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileItem.tsx
index eb86aae26..61d85f737 100644
--- a/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileItem.tsx
+++ b/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileItem.tsx
@@ -21,6 +21,7 @@ export type PopoverFileItemProps = {
   isAttachedToNote: boolean;
   handleFileAction: (action: PopoverFileItemAction) => Promise<boolean>;
   getIconType(type: string): IconType;
+  closeOnBlur: (event: { relatedTarget: EventTarget | null }) => void;
 };
 
 export const PopoverFileItem: FunctionComponent<PopoverFileItemProps> = ({
@@ -28,6 +29,7 @@ export const PopoverFileItem: FunctionComponent<PopoverFileItemProps> = ({
   isAttachedToNote,
   handleFileAction,
   getIconType,
+  closeOnBlur,
 }) => {
   const [fileName, setFileName] = useState(file.name);
   const [isRenamingFile, setIsRenamingFile] = useState(false);
@@ -93,6 +95,7 @@ export const PopoverFileItem: FunctionComponent<PopoverFileItemProps> = ({
         isAttachedToNote={isAttachedToNote}
         handleFileAction={handleFileAction}
         setIsRenamingFile={setIsRenamingFile}
+        closeOnBlur={closeOnBlur}
       />
     </div>
   );
diff --git a/app/assets/javascripts/components/Button.tsx b/app/assets/javascripts/components/Button.tsx
index 516d416fe..8ac16a5be 100644
--- a/app/assets/javascripts/components/Button.tsx
+++ b/app/assets/javascripts/components/Button.tsx
@@ -25,6 +25,7 @@ type ButtonProps = {
       | TargetedEvent<HTMLFormElement>
       | TargetedMouseEvent<HTMLButtonElement>
   ) => void;
+  onBlur?: (event: FocusEvent) => void;
   disabled?: boolean;
 };
 
@@ -34,6 +35,7 @@ export const Button: FunctionComponent<ButtonProps> = forwardRef(
       type,
       label,
       className = '',
+      onBlur,
       onClick,
       disabled = false,
       children,
@@ -46,6 +48,7 @@ export const Button: FunctionComponent<ButtonProps> = forwardRef(
     return (
       <button
         className={`${buttonClass} ${cursorClass} ${className}`}
+        onBlur={onBlur}
         onClick={(e) => {
           onClick(e);
           e.preventDefault();